So a Guy Walks Into a School in a Skirt . . .

By ALISON LEIGH COWAN

Published: November 13, 2003

NEW MILFORD, Conn., Nov. 11—
Even now, no one is entirely sure why Kevin Dougherty, 15, showed up for school one day last month wearing a floral skirt and matching scarf tied jauntily around his neck. Pantyhose, eye shadow and lipstick completed the look.

When administrators at the high school sent him home for refusing to change clothes, he left, but also called the local newspapers and the Connecticut Civil Liberties Union. Now, nearly two weeks later, the town is still buzzing, though there is no consensus whether it was simply a defiant Halloween costume, as school officials and their lawyers maintain, or a constitutionally protected act of protest, as Kevin says.

Since neither side is showing signs of budging, the dispute seems headed to court.

School administrators referred all calls for comment to the interim superintendent, JeanAnn Paddyfote. She said Wednesday that she could not discuss details of the case but that nothing about it caused school officials to rethink the ban on what it calls disruptive clothing.

Dressed in his usual khakis and Shetland sweaters, Kevin Dougherty does not look like much of a rebel. Soft-spoken, he plays drums for the school band, takes in unwanted dogs, and mows lawns for pocket money.

He does have a history of asserting himself in unexpected ways against a school system that he believes infringes on students' civil rights.

His earliest taste of that, he said, came in the eighth grade when he was asked to design a political cartoon in civics class. He drew a Roman Catholic priest with a caption saying, ''Reach out and touch someone.'' He said the teacher asked him to redo it because it was offensive, so he brought in a blank sheet of paper the next day to make a point and got a zero on the project.

A more recent clash took place in mid-October on Homecoming Week, when students were advised to come to school as a famous person. He came as Hitler. He said school administrators made him remove the swastika and trench coat, so he was mistaken for Charlie Chaplin.

His father, Brian Dougherty, said he thought his eldest son might have shown poor taste but should have been let alone.

Students were told over the public address system in late October that they were to come to school on Oct. 31 in ''proper attire'' rather than in Halloween costume, and, though it is far from clear whether the announcement had anything to do with the Hitler outfit, Kevin said he decided then and there to wear a skirt or dress to school that day.

The dress code does prohibit clothing that is distracting or advertises ''sexual activity or preference,'' but he thought traditional women's clothing would qualify as ''proper attire,'' he said, since it is on display on school grounds on most weekdays.

Assembling the outfit was harder than it looked. His parents are divorced and he lives with his father, so the closets had nothing to offer.

A neighbor told him he might be a size 14 dress. His father drove him to a local thrift store, where he paid $7 for a below-the-knee skirt, jacket, scarf and blouse. He spent $9 at Wal-Mart for some makeup and one-size-fits-all pantyhose.

In composing his outfit, he said, he imagined what Dr. Paddyfote might wear to work. He said he might have used Ellamae Baldelli, the school's principal, as a model, but could not because she often wore a suit and tie.

Mr. Dougherty spoke with Ms. Baldelli on Oct. 31 and secretly recorded the conversation. (In New York, such a recording would be legal, but in Connecticut both parties must consent, lawyers say.) According to a transcript made by Mr. Dougherty, Ms. Baldelli said that the school did not permit cross-dressing and that although girls were permitted to wear slacks, ''there would be some girls that would be offended'' by a boy in a skirt.

The Connecticut Civil Liberties Union told the school in a letter dated Nov. 3 that Kevin's ''expressive conduct'' was ''squarely within the protection of the First Amendment.'' It also asked the school to ''allow both girls and boys the option of wearing a dress to school.''

There is no indication that other high school students are either riveted by Kevin's act or sympathetic to it.

''This whole entire thing was done for attention,'' said Vince Ducibella, a sophomore, barely looking up from his homework.

Kevin disagrees. If doing it again would help make the school system reconsider its policies, he said he would.

Then he added, just ''not the pantyhose.''

Photo: Kevin Dougherty and the outfit he wore to school on Halloween. (Photo by Don Hogan Charles/The New York Times)